“And Yaakov dispatched messengers before him to Eisav his brother, toward the land of Se’ir, the field of Edom.” (Bereshis 32:4) 

Why did Yaakov initiate this contact with Eisav? Would it not have been preferable to merely avoid Eisav, in light of the fact that Yaakov was anyway not planning to travel to Eisav’s territory, the land of Se’ir, but was instead on the way to his father Yitzchak in Chevron (Hebron)?

The Ramban (Ibid.) explains that Yaakov would need to travel in the proximity of Eisav’s territory, or perhaps even though it, in order to reach Chevron, and hence there was great apprehension on the part of Yaakov that Eisav would arise and pursue Yaakov and his family as they approached. Yaakov therefore needed to address this concern in advance.

The Ramban then cites Bereshis Rabbah (45:3), which features an opinion that Yaakov was wrong to initiate this contact with Eisav: 

“Rav Huna commenced (his exegesis of the parshah with the verse): One who gets involved in an argument that is not his is akin to one who grabs the ears of a dog (unnecessarily inciting it).’ (Mishlei 26:17)… The Holy One, blessed be He, said to Yaakov: ‘Eisav was going on his own way, and you proceed to contact him…?’”

According to Rav Huna, what was Yaakov’s rationale for initiating communication with Eisav? Yaakov was obviously not a fool; he was an immensely great and wise man, and everything he did was extremely calculated. What was Yaakov’s motivation for contacting Eisav, even though it ultimately ought not have been done, according to Rav Huna?

Prior to this point, Yaakov had been in Charan, dependent on the employment of Lavan and living in exile, and Eisav did not perceive Yaakov as a threat. However, once Yaakov began his trek toward Eretz Yisroel, as a wealthy and independent force with which to be reckoned, matters were vastly different. It is true that the last thing in the world that Yaakov sought was to battle Eisav; nonetheless, Yaakov’s return to Chevron, the seat of the family patriarchy, as the prosperous and prestigious leader of a large clan, might trigger aggression on the part of Eisav, who dwelled not far away. I think that this is what was going through Yaakov’s mind, such that he felt the need to preempt belligerence by Eisav as he (Yaakov) approached. When one also considers that Yaakov, rather than Eisav, had obtained Yitzchak’s berachos, which expressed authority and substance, it would appear pretty clear to Eisav that Yaakov was returning to Chevron not simply to be with his aged father Yitzchak, but rather to assert himself at the seat of the family patriarchy as the next leader, succeeding Yitzchak and supplanting Eisav as the prospective headman. Even though Yaakov did not exactly have such plans, he assumed that Eisav would not take kindly to the images that were being conjured up, and Yaakov determined that he therefore needed to reach out to Eisav in order to prevent an onslaught.

Yaakov’s calculus seemed so accurate – where did he go wrong, according to Rav Huna?

Eisav was focused on the material here and now; Yitzchak’s berachos meant enrichment and physical domination, and they were not viewed by Eisav as of spiritual worth or utility. Once Eisav established his seat of power in Se’ir and had amassed a mammoth abundance of wealth, territorial control and authority, the notion of serving as the spiritual successor of Yitzchak in Chevron was irrelevant and of no interest. Eisav had no need for it, just like he had no need for the spiritual leadership embodied by the bechorah (birthright) which he sold to Yaakov so many decades prior. Yaakov’s error, according to Rav Huna, was that as a spiritual person, he viewed the situation through a lens of sanctity, and assumed that Eisav, despite his roughness and enmity, would surely be jealous of Yaakov assuming the role as the next of the Avos (Patriarchs) in Chevron. For Yaakov rather than Eisav to be vested with this holy position would evoke the ire of Eisav, Yaakov thought. But in truth, becoming Yitzchak’s spiritual successor was worthless to Eisav, who resented Yaakov only for the physical aspects of the berachos which Eisav felt Yaakov had stolen. Yaakov’s religious journey back to Chevron would not have bothered Eisav; Eisav was better left alone, like a sleeping dog that one should let lie, and ought not have been incited, maintained Rav Huna.

The great struggle between Yaakov and Eisav commenced in Rivka’s womb and signaled a clash over the inheritance of the physical and spiritual worlds. (Rashi, from Medrash, on Bereshis 25:22) The radical differences in attitude toward these two worlds on the part of Yaakov and Eisav explain the perplexing dynamics between these two men in our parshah, and the dramatic interactions between their progeny and ideological heirs for the ensuing millennia.